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S. A. Yamashkin, O. V. Pozdnyakova, M. A. Yurovskaya

Synthesis of pyrrolo[3,2-f]quinolines via reaction of 2,5-dimethyl- or, 1,2,5-trimethyl-6-aminoindoles with β-ketoesters


Reaction of 2,5-dimethyl- or 1,2,5-trimethyl-6-aminoindoles with ß-ketoesters (methyl and ethyl acetoacetates, diethyl oxaloacetate) was found to proceed chemoselectively via interaction between amino group of indole and carbonyl function of ketoether leading to enamines formation. In contrast to enamines, synthesized from similar aminoindoles and β-diketones, enamines from β-ketoesters can easily undergo thermal cyclization furnishing pyrrolo[3,2-f]quinolines with angular catenation of rings.
Key words: 6-amino-2,5-dimethylindole, 6-amino-1,2,5-trimethylindole, methyl acetoacetate, ethyl acetoacetate, diethyl oxaloacetate, pyrrolo[3,2-f]quinolines.
Moscow University Chemistry Bulletin.
2014, Vol. 55, No. 1, P. 36

Copyright (C) Chemistry Dept., Moscow State University, 2002
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